Little Black Midi Dresses
Little black midi dresses are the ultimate game-changer—effortlessly chic, endlessly versatile, and always ready to make you the main character. Whether you’re stirring up a little mischief on girls’ night or owning the spotlight at your next big event, these dresses have your back. Slip into one and instantly level up your confidence—because with a little black midi dress, you’ll never have to worry about what to wear again.
$49.90
A chic black mesh midi dress with a mock neck, scarf accent, and flirty side slit.
$42.90
A sleek black knit midi dress with a high slit, cowl neckline, and spaghetti straps.
$59.90
A glamorous black satin midi dress with a cowl neckline and adjustable spaghetti straps.
$36.90
An elegant black off-the-shoulder midi dress with a bodycon fit and flared hem in stretchy knit.
$59.90
A black satin midi dress with a pleated cowl neckline, midriff cutout, and high side slit.
$38.90
A black sleeveless ribbed knit midi dress with a V-neckline and chic high front slit.
$39.90
A sultry black one-shoulder bodycon midi dress crafted from smooth, stretchy double-lined knit fabric.
$49.90
A black satin midi dress featuring a cowl neckline, ruched front, bodycon fit, and sultry slit.
$48.90
An elegant black off-the-shoulder midi dress with ruched sides and a flattering bodycon fit.
$54.90
A black crepe glitter knit midi dress with a form-hugging silhouette and chic wrap hem.
$46.90
A chic black bodycon midi dress with a square neckline and stretchy double-lined knit fabric.
$36.90
A black knit midi dress with a sleeveless square neckline, ruching, and pleated mermaid silhouette.
$39.90
A captivating black floral mesh maxi dress with a lace-up back and flared hem.
$46.90
A strapless black satin midi dress featuring pleating, a high side slit, and a form-hugging fit.
$9.97 $42.90 77% off
A chic black strapless midi dress with a cowl-draped neckline and asymmetric hem for allure.
$35.90
A sleek black strapless midi dress crafted from smooth, stretchy knit fabric with padded bra cups.
$39.90
A sultry black bodycon midi dress featuring a floral velvet burnout texture and lace-trimmed neckline.
$38.90
A curve-flaunting black midi dress with a plunging cowl neck and open tie-back design.
$35.90
A black knit midi dress featuring a halter neckline, crisscross back, and flattering bodycon silhouette.
$44.90
A black midi dress with a floral flocked velvet pattern, halter neckline, and high side slit.
$44.90
An elegant black knit midi dress featuring an off-the-shoulder neckline and a pleated wrap-front slit.
$9.97 $49.90 80% off
An elegant black mesh midi dress with ruched sides, sheer sleeves, and a tiered ruffled hem.
$29.97 $59.90 50% off
A chic black strapless bodycon midi dress with a front slit and flexible boning.
$36.90
A sleek black knit midi dress with a halter neckline and flared mermaid silhouette.
$9.97 $49.90 80% off
A strapless black woven midi dress featuring a color block bodice, flowy hem, and hidden pockets.
$59.90
A sultry black strapless velvet midi dress with a ruched bodycon fit and side slit.
$49.90
An off-the-shoulder black midi dress featuring mesh-lined fabric, ruched bodycon silhouette, and a bold side slit.
$39.90
A sleek black knit midi dress featuring a ruched bodycon silhouette, sleeveless V-neckline, and spaghetti straps.
$9.97 $39.90 75% off
A black glitter knit midi dress with a cowl neckline and mermaid silhouette for formal occasions.
$54.90
An alluring black velvet midi dress with a flirty bust cutout and ruffled hem for cocktail events.
$52.90
A black knit midi dress featuring lace trim, flirty cutouts, and a high side slit.
$29.97 $59.90 50% off
A black glitter knit midi dress with an off-the-shoulder neckline and chic ruched details.
$56.90
A versatile black knit bodycon midi dress with a convertible neckline for multiple styling options.
$55.90
An elegant black mesh midi dress adorned with mini rhinestones and faux pearls for a glamorous look.
$42.90
A black knit midi dress featuring a front-tie bust, underbust cutout, and high front slit.
$46.90
A strapless black bodycon midi dress in structured ponte knit with a sweetheart neckline and vertical seams.
$20.97 $46.90 55% off
A black floral midi dress with a corset bodice, sweetheart neckline, and flirty front slit.
$59.90
A black crepe mermaid dress with a square halter neckline and elegant high front slit.
$26.90
A sleek black knit midi skirt featuring a high-rise waist, bodycon fit, and center back slit.
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Achieve a perfectly stylish everyday look with this sleeveless ribbed knit midi dress! Designed with a comfortable ribbed knit fabric offering plenty of stretch, it features a V-neckline, spaghetti straps, a midi-length hem with a chic high front slit, and a form-hugging silhouette. Pair with a cropped denim jacket and clear mules. Fit & FeaturesStretchy ribbed knit fabric, V-neckline, Spaghetti straps, High front slit, Form-hugging fit, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Perfectly Stylish Sleeveless Ribbed Knit Midi Dress in Black | Size: M | Knit Fabric
Channel the chic fall vibe in this ditsy floral woven midi dress featuring a sleeveless sweetheart neckline with a ruched bust and tie-front detail, thin tank shoulder straps, and a corset-style bodice. The high waist leads to a flowy A-line silhouette accented with a high-cut front slit. Fit & FeaturesDitsy floral-printed woven fabric, Sweetheart neckline, ruched bust, tie-front detail, underwire bust, Thin tank shoulder straps, Corset-style bodice with piping, high waist seam, Hidden side zipper and hook-eye closure, High front slit, Midi-length A-line fit, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Chic Fall Vibe Ditsy Floral Corset Midi Dress in Brown | Size: S | Woven Fabric
Windsor Thriving Blooms Corset Floral Slit Midi Dress in Black
$20.97 $46.90
55% off
Thrive with sweet energy in this floral midi dress perfect for brunches or dates! With a corset bodice that snatches your waist and a flirty front slit, this a-line dress will captive everyone. Pair with a necklace. Fit & FeaturesDitsy floral print, woven fabric, Wide shoulder straps, sweetheart neckline, Corset bodice, Side pockets, A-line silhouette, front slit, Midi-length hem, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Thriving Blooms Corset Floral Slit Midi Dress in Black | Size: S | Woven Fabric
Capture hearts with your sweet look in this airy eyelet knit skater dress. You'll adore the flowy feel of the fit-and-flare silhouette. Fit & FeaturesEyelet knit fabric with knit lining, Sleeveless square neckline, underbust seam, Adjustable spaghetti straps, Skater silhouette, Mini-length hem, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Sweet Look Eyelet Knit Skater Dress in White | Size: M | Knit Fabric
Create a cute picturesque 'fit in this corset A-line midi dress! The corset bodice and lace-up back add a touch of allure to the sweet silhouette. Fit & FeaturesWoven fabric lined with stretchy knit, Sweetheart neckline, tie-front detail, Thin adjustable straps, Corset bodice, lace-up back, High waist seam, Midi-length A-line silhouette, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Picturesque Cutie Corset Lace-Up A-Line Midi Dress in Light Blue | Size: L | Woven Fabric
Show off your smooth moves in this strapless bodycon midi dress perfect for dressing up or down for any occasion! Fit & FeaturesRib knit fabric, sewn-in knit lining, moderate stretch, Strapless neckline, Side slit, Bodycon silhouette, Midi-length hem, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Smooth Talker Strapless Bodycon Midi Dress in Light Blue | Size: L | Knit Fabric
This sleeveless ribbed knit midi dress features a striking V-neckline and bodycon fit with a front slit detail for movement. Perfect for layering with a jacket and heels. Fit & FeaturesStretchy ribbed knit fabric, V-neckline, Spaghetti straps, Front slit, Midi-length bodycon fit, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Toasty Sweetheart V-Neck Bodycon Knit Midi Dress in Chartreuse | Size: L | Knit Fabric
The perfect chic sleeveless midi dress for grabbing dinner downtown! Crafted from smooth knit fabric, this crew neck dress boasts curve-accentuating ruched seams along the bodycon silhouette and a sleek midi-length hem. Pair with kitten heels and a clutch. Fit & FeaturesSmooth knit fabric, stretchy knit lining, Sleeveless crew neck, Side ruched seams, Bodycon silhouette, Midi-length hem, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Dinner Downtown Sleeveless Ruched Midi Dress in Brown | Size: M | Knit Fabric
On A Vacay Strapless Tropical Slit Maxi Dress
$19.97 $39.90
50% off
From sunny vacations to island getaways, this tropical maxi dress is destined to go with you on your next trip! Fit & FeaturesTropical palm print, mesh fabric lined with stretchy knit, Strapless neckline, Form-hugging silhouette, High side slit, Maxi-length hem, Runs true to size, Free Shipping on All Orders Over $75. | Windsor On A Vacay Strapless Tropical Slit Maxi Dress | Size: XS | Mesh Fabric/Mesh Fabric
Windsor Blissful Cutie Halter Cutout Skater Dress in Yellow
$9.97 $46.90
79% off
Get swept off your feet in this cute skater dress for any casual occasion! With its halter neckline and cutout bodice, this dress is designed to show off your figure, while the ruffled mini-length hem adds a flirty touch. Fit & FeaturesGauze woven fabric, woven lining, Halter neckline with spaghetti strap ties, Stretchy smocked bust, Cutout bodice, Ruffled skater silhouette, Mini-length hem, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Blissful Cutie Halter Cutout Skater Dress in Yellow | Size: L | Gauze/Woven Fabric
Little Black Midi Dresses
Every Windsor girl knows the power of a little black midi dress—it’s the ultimate style sidekick, always ready to turn any moment into a main character moment. Whether you’re making an entrance at a rooftop party, owning the dance floor, or just strutting into brunch like you’re on a runway, a midi little black dress is the definition of versatile glam. The midi length is that sweet spot—long enough to keep things sophisticated, but short enough to still show off those killer shoes and a bit of leg. It’s the kind of silhouette that flatters every curve, hugs you in all the right places, and moves with you (because let’s be honest, we’re not standing still for long). When you slip into a black midi, you’re not just getting dressed; you’re setting the tone for whatever adventure comes next—whether that’s a spontaneous road trip, a last-minute dinner date, or a girls’ night that turns into a sunrise breakfast.
Shopping for a midi little black dress is all about finding your vibe. Are you channeling classic Hollywood with sleek lines and minimalist details, or are you here to make jaws drop with daring cutouts, luxe fabrics, or a flirty slit? The beauty of the black midi is that it can be as extra or as understated as you want. It’s the perfect blank canvas for your boldest accessories—think chunky gold hoops, a neon clutch, or those strappy heels you’ve been dying to show off. And if you’re on the hunt for the perfect gift, trust: a black midi is the ultimate “I got you” present for birthdays, bachelorettes, or just because your bestie deserves to feel like a star. There’s something about gifting a dress that feels personal, like you’re handing over a ticket to confidence and unforgettable memories. Plus, with all the different necklines, sleeve lengths, and details out there, you can pick a style that matches her energy—whether she’s the queen of understated chic or loves to turn every sidewalk into a catwalk.
Let’s be real: the best part of owning a midi little black dress is how it fits into every single plan—planned or unplanned. You can throw on a denim jacket and sneakers for a coffee run, then swap in a blazer and pumps for that big meeting, and still be ready to hit the city lights by nightfall. The right midi hugs your curves, gives you that “I woke up like this” confidence, and looks just as good when you’re twirling on the dance floor as it does when you’re perched at the bar, sipping something bubbly. And if you’re craving a little extra drama, don’t miss out on the magic of ruching—check out our Black Ruched Midi Dresses for styles that sculpt, flatter, and serve major attitude. At the end of the day, a black midi isn’t just a dress—it’s a whole mood, ready to back you up no matter where the night takes you. So go ahead, make space in your closet for a piece that’s always down for a little fun and a lot of compliments.